Heartless?
by pinklips
Summary: Chuck Bass has finally said those three words and everything is perfect again in the Upper East Side. But somebody is pregnant and Chuck is the father. Will it be too late for Chuck and Blair? Surely the Queen Bee will not go down without a fight..
1. Prologue: He Makes Good Girls Go Bad

_**Disclaimer: I do not own Gossip Girl nor the song Heartless by Kanye West. Because if I did, I would be hella rich right now :P First chapter is RATED M. Don't read if you don't like sex scenes. **_

_**Author's Note: So I changed the prologue. This takes place after Season Two's "The Wrath of Con". Figured this one would be better. It's my first time to write a sex scene and a fan fic so do let me know what you think, please? I love your reviews. Thank you. :)**_

**XOXO**

**Prologue: He Makes Good Girls Go Bad**

To say that Chuck Bass is lonely is definitely an understatement. And as he sat on his thousand dollar chair with a glass of scotch in one hand, the feeling of loneliness couldn't have been more evident. Not that he was alone by any chance; a girl was currently sleeping soundly on his bed. Unfortunately, she wasn't the girl he wanted to be with at the moment or possibly, forever. To him, she was just another nameless girl who made his night a little more bearable.

As soon as the high from having sex was gone though, Chuck found the same feeling of loneliness creeping back. It scared him of course, to be alone, and to have anyone know that he actually felt lonely. Come on, Chuck Bass, lonely?

What's worse than having people know he's lonely? It's being vulnerable in front of others. Not even in front of step-sisters. For Chuck, being vulnerable equals to being weak. Blair was the only person he had let in. But due to the events that happened earlier, he couldn't help it. And he was just that – vulnerable in front of Serena. As he basked in the quietness of the early morning, he kept on thinking about the conversation he had with Serena.

"Chuck, why did you just do that?" she asked.

"Because I love her and I can't make her happy." He replied and that was that. No other explanation.

It was hard to imagine that just a few hours ago, he let Blair Waldorf walk out of his life. It's what he wanted, right? To push her away. To do what's best for her. It was a noble thing to do, especially for Chuck Bass.

But boy did it hurt. It hurt so bad that he had to practically shove the tears back into his eyes from falling down. Men didn't cry. Especially not Chuck Bass. But Chuck knew it was time to move on. So he sucked it up and did what he thought was best to cure his broken heart. He partied. To justify it, he thought of another excuse. It was supposed to be just a business affair: he bought back Victrola and wanted to see how the place was doing. It was his first big business decision after his father died and he wanted to make sure it was a good choice.

The moment he stepped in the club, though, he knew that it was a bad idea. It was right there on the stage that he saw Blair in a different light. The events that happened after.. well, that was the start of something. His life turned upside down after the limo ride with Blair. Suddenly life wasn't just this big sexfest with anything _fuckable._ It had meaning, it had excitement. He was looking forward to actually getting up in the morning and seeing her: seeing her smile, hearing her laugh. He found himself having feelings he never knew existed in him. A soft side, even. Chuck Bass realized that he wasn't this heartless beast he thought he was.

All of a sudden, the memories came flashing back that it was driving him insane. He almost left, but quickly decided against it. He was stronger than that, he shouldn't let Blair control him or how he lives his life. Especially now that she's gone.

As he made his way to the VIP area, that's when he saw _her_. She looked out of place in Victrola, like a little child in rehab. Yet she looked as though she belonged there. She had an innocent aura that was impossible to miss, with her wide almond shaped black eyes. But her lips contradicted that. It was painted with a very bright and sultry red.

At first she reminded him of Blair, but then again, he thinks that way with every woman he meets. He didn't get to see her that much, though. For a moment, their eyes seemed to have met – until the club bouncers shooed her away. She bumped into him, and they thought she was trying to attack him. They quickly whisked him away before he could even talk to her.

But as luck would have it, he saw her again. Drinking alcohol in plastic cups of all things. That was the moment he decided to make her the conquest of the night. It didn't help that she looked very hot in that outfit of hers, even though her body was something he normally wouldn't go for. She was chubby and overweight, but he was impressed at her boldness to wear such a daring thing. Her attitude definitely added to the turn on.

So he came up to her, got drunk, took her home. One thing led to another, and the next thing he knows, it was all over. He found it comforting at first, not having to sleep alone, but quickly regretted it. She isn't the one he wants next to him. She isn't the one he wants to see the minute he wakes up.

_But she isn't Blair_.

It was three o'clock in the morning already, and he was looking intently at the girl sprawled on his bed. He had long forgotten her name already and he was wondering why the hell he did he sleep with her in the first place.

And then he remembered. Because she isn't Blair. She was the opposite even. Too much of a goody two shoes that he wondered why she was even in the club. That made it easy for him to decide to sleep with her, thinking that he could do it without thinking of Blair.

But he was wrong, the whole time they were fucking, he was thinking of Blair. Pretended it was her that he was doing. He almost groaned Blair's name in ecstasy at some point even.

He finished his scotch and decided to go back to bed but it was impossible to sleep. The scotch was making his body hot all over, and thoughts of Blair weren't helping either. Again, he looked at the naked girl in his bed and decided that he was going to fuck her for the third time that night. He might as well have his fun while she's here. At least pretend it was Blair sleeping over and wanting him.

The girls back was turned to him, so he kissed her neck while feeling her large breasts. It was another factor that drawn him to her, he was always a sucker for breasts. He played with her nipples gently at first and then kissed her neck some more. She awoke with a gasp as Chuck's hands moved to caress her pussy. She was hesitant at first, perhaps because the effects of the alcohol were wearing off, but still didn't stop him when he inserted a finger inside her.

He was getting harder and harder already as he kissed her lips. The girl was faced him and he sucked and bit her erect nipples violently. Her moans started to get louder, and Chuck found himself getting more turned on. So she liked it rough, he thought.

He was overcome with lust already, and the intoxicating smell of sex and alcohol filled the room. He climbed on top of her and did something he normally didn't do. He looked at her hard. His piercing brown eyes illuminated by the moonlight from the Manhattan skyline view in his room. The setting couldn't have been more romantic, if only they were actually _making love_ as opposed to just sex. Then he kissed her, a soft sweet kiss on the lips that made the girl smile. It was a nice contrast from the way he roughly handled her nipples, she thought. He kissed her again, harder this time. It was a deep, passionate kiss that surprised even Chuck. A kiss that literally left them gasping for air. After a few more kisses, he couldn't take it anymore and got ready to enter her.

"You ready?" he asked, still gazing at the girl. She merely nodded.

He didn't know what was wrong with him, he wanted to fuck her so badly. Mostly to forget Blair, to distract himself. And yet every time he closes his eyes a mental image of Blair lying down, naked, was all he could see. But he was still a man with needs, with or without Blair. In the end, he gave in to his horniness.

He entered her in one quick, violent motion and groaned. She was tight, and it was driving him insane. He pulled out slowly and entered her quickly again. This time it was her turn to moan, and he felt her tighten her grip his shoulders more tightly.

He pounded her hard until he couldn't take it anymore. He came so intensely that he almost passed out. Their tangled, sweaty bodies still one, as they panted and tried to catch their breath. He rolled off her and readjusted his pillow, to his surprise, the girl curled up to him and lay on his arm. He looked at her and kissed her, gently this time. She quickly fell asleep as he stroked her hair. He kissed her forehead and closed his eyes.

The last thing he remembered before he fell asleep was Blair Waldorf. The only person he really wants to spend the rest of his nights, mornings, and everything in between with.


	2. Chapter 1: The Girl With Red Lips

**Chapter One: The girl with red lips**

_Jess's Point of View_

"_Fro once in your life, do something exciting. Or fun. You owe it to yourself, Jess." _My sister's words echoed in my head long after she said them. Here I am, sitting down on my bed while looking out the window. I'm pondering on whether or not she's right. Am I really that uptight?

No. Of course not.

She is so wrooong. Dead wrong. Of course I'm not uptight. I do fun things, exciting even. I'm daring. Yeah, damn right I am. You know what I'll do? I'm going to prove her wrong.

Tonight.

I am so going to join my sister tonight. Yup, the same sister who tells me to loosen up. She's older than me, being 22 already, but her mental age is like 16 years old. I'm turning 18 in a few months so I guess I am older than her in so many levels. I can't help it.

I wasn't always like this, though. I used to be dependent on my parents, especially my mom. Ever since she got married again though, things changed. I like my stepfather but I I felt like an outsider in my own home. So I packed my bags and went to New York to live with my dad. But he had a crazy schedule and we kept on moving back and forth that it was really hard on my part.

Finally, when I turned 17, my parents decided that it was time for me to have a stable environment. I was left at the care of my sister, Hannah. Rather, I was left to care for Hannah. I guess she's a lot like my parents – carefree, fun-loving, and basically just happy people. So that's how I turned into this uptight, zombie freak with no concept of fun. If I wasn't keeping tabs on things, or being their mom as she sometimes joked, I swear our whole household will collapse.

Between you and me, I actually feel okay with this already. I love taking care of people, cooking, baking, and other "mom" jobs. It's like my comfort zone, and I don't like leaving it.

But tonight everything's going to change. Goodbye, boring old Jess. I was looking through my closet for something to wear when Hannah suddenly came in.

"Ready for tonight, little sis? You will be smoookiiin."

"Are you sure you'll take me? I am a minor, you know."

"What am I like an idiot? Of course you're not. Here." She said as she handed me this card like thing.

Oh. It's a fake id. Let's see now.. My name is Hannae Marshall. I'm 21 years old and I'm legal.

"Hannae? What the hell were you thinking?"

"Hannah. Hannae. Isn't it cute? We can be twins."

"Yeah, like anyone will ever believe you."

Hannah, the girl of long legs and gorgeous black/brown hair, and me, the plainest jane ever? Unlikely.

"Of course they will. Now honey, give me a hug. Oh my god, your first fake id. I think I'm going to cry." She said as she pretended to wipe a tear.

"Hush, hush, big sister. It's okay."

"Now, go get ready. We'll leave at around 9 ish. I'm going to do my usual beauty routine now."

"But isn't that too late?"

"Honey, the party starts at midnight. Relax."

Right. I knew that.

**xoxo**

By 8:30 sharp, I was beyond ready. I was having second thoughts, and all the waiting was doing nothing to excite me. I already had dinner, showered, got dressed, and I have even put on make-up. I may be a boring, overweight girl, but I do love dressing up and putting make-up on. What can I say, I am a girl.

I'm wearing my most flattering outfit tonight. I really think it compliments my tan and not quite fair skin ( I blame it on the fact that my dad is Caucasian and my mom is Asian). A black mini dress that shows off my shapely legs (I think they're my best asset!), black open toe heels, a long pearl necklace, and of course, red lips. I love highlighting my lips, and I think red lips are so glamorous. I dare to be more adventurous, right? I just wish I didn't get a haircut. Now my black hair's too short to be curled. Oh well, I'll just rock this 'do anyway.

Gosh, I feel like a completely different person. I don't look like myself. I don't dress like this and I kind of feel like a hooker. A classy hooker, if there's even such a thing. I wish Hannah would hurry up now. I can't wait to get this over with.

I bet it's going to be really boring. What happens in a club anyway? Dancing, maybe. And drinking. God, why would someone want to waste their time in places like that? What am I gonna do there? I feel like this is a bad decision already. Maybe it's not too late to back out.

"Hannah?" I called out.

"In a minute, Jess. Can't you wait?"

"I think I feel a flu coming. Maybe I should just stay here and rest."

Silence. Uh oh. Is she mad? Damn.

"No! You wouldn't dare! Jessica Antoinette Gregory. You will not sit this one out. You will go with me and party the night away. Understand?"

This is the big sister part. She can be so bossy.. and scary at times.

"Okay, but can you hurry up?"

A few minutes later, Hannah finally emerged from the stairs. She looks breathtaking, as usual. She's in a sexy white mini dress that totally enhances her tan, really high stilettos, and her signature smoky eye and pale lips make up. Wow. She looks like a supermodel. I'm sure all the boys will be wanting her attention tonight.

"Wow little sis, I have to say, you look awesome. Really."

"Me? But look at you! You look like a supermodel. I'm sure you'll be the center of attention."

"Sheesh. Who cares? Tonight, I'm with you! And I have to say this again, you really look hot."

"Thanks."

"Look's like someone is getting laid tonight!" Hannah said with an evil glint in her eye.

Yeah, like that will ever happen.


	3. Chapter 2: Those Brown Eyes

**Chapter Two: Those Brown Eyes**

_Jess's POV_

I can't believe Hannah planned all of this! We finally reached the club (supposedly the hottest one around in NY) and I was surprised to find two of my closest friends waiting for us.

"Surpriiiiise!" Catherine exclaimed as soon as she saw us.

"What the hell are you guys doing here?"

"What, can't we have fun, Little Miss Goody Two Shoes?" asked my other friend, Lance.

"Oh really? So I'm a goody two shoes. Well, then you're a party whore." I retorted, pretending to be pissed.

"Honey, I put the whore in party whore!" he replied as we laughed our heads off.

Catherine and Lance was the first people who were nice to me on the first day of school. They've been best friends since elementary, and they couldn't be more alike. Catherine Carr, the daughter of a high-powered attorney, was raised by a series of nannies. Her parent's divorced when she was young, and her dad practically lives in his office. She's just like everyone else in school, beautiful, tall, and rich. You would think that because she's all that, she would be hanging out with the popular girls and stuff. But no, _they _decided that she wasn't pretty enough to hang with them.

Then there's Lance. The first thing people notice about him is that he's such a handsome boy. He always looks as though he stepped out of the pages of GQ. The second thing people notice about him is that he's gay. The first time I saw him and Cath together, I thought they were an item. That is, before Lance told Cath that her new Marc Jacobs Stam bag in red was fabulous. But Lance is cool. Truth be told, I'm closer to him than to Cath.

As I make my way through the end of the long line, I noticed that none of them were behind me.

"Jess! Where are you going?" Hannah called out.

"To the end of the line. Who knew a lot of people would want to enter the club?"

Hannah just rolled her eyes and grabbed my hand.

"We're not lining up, you duffus."

Right. Of course I knew that.

We walked past the people waiting in line and went straight to the main entrance. The bouncer lifted the red velvet rope that separates the crowd from the club and let Hannah in. I was about to follow when the bouncer stopped me.

"End of the line, miss."

What? That's a bit insulting. I spent a long time preparing myself tonight. Don't I look club worthy enough?

"It's okay, Damien. She's with us." Catherine told the bouncer.

"Is that so Miss Carr? Okay. Get in." he told me as he lifted the rope once again.

"Sorry about that, miss."

"Yeah? Well, talk to my lawyer." I said as I breezed past him.

As soon as I got in, I immediately regretted saying that. I shouldn't have done that. When did I become so rude? I must've hurt the poor bouncers feelings. I mean, he was just doing his job. It wasn't his fault. I must go out there and apologize.

I walked back to where he was and tapped his shoulders.

"I'm sorry. I shouldn't have done that. I want you to know that I don't do that very often. That was rude and I'm really sorry. It was a mistake on my part."

There. I'm completely being the bigger person. Wow, since when did I become so mature? I stand there, feeling proud of myself, awaiting his reply. Surely he'll forgive me. He was looking at me, totally weirded out as if he didn't know what I was talking about.

Oh good grief. I'm such a fool. Of course he must get this all the time, people threatening to sue him.

"Right. I'll just.. I'll just.. umm.. go back inside."

Why do you have to be such a goody two shoes, Jessica Gregory? Sheesh.

**XOXO**

In the seventeen years I've been living, I've only gotten drunk twice. Once during Christmas when I was 13, and the other time was when Hannah graduated from High School. Both times we were just at home, and thus heavily supervised. This is my first venture out into the real world of clubbing.

Being a club virgin, my _kind_ friends volunteered to order the drinks for me. It isn't even midnight yet but so far I've drank three alcoholic drinks already. The sex on the beach, blowjob, and another one. Yeah, I do not even remember the name. You want to know what's worse? I'm drunk already. I've broken 4 glasses already. I know. Shame on me.

But that's not my fault, right? I've been dancing the night away (Who knew I could even dance?) and my heels are killing me already. My friends have drunk waaaaay more than me but it is only Catherine who's plastered. My sister is MIA but I last saw her dancing with some of her co-workers.

"This round's on me!" Lance announced as we made our way to the bar. He was kind of red already but he could still talk straight.

"Are you sure baby boy? Cath looks beyond drunk. I think we should take her home."

I'm losing my inhibitions little by little and I'm afraid of what I'm going to do next. I just want to go home.

"You wait here. I'm taking her to her car."

"You're not going to let her drive in that condition, right?"

"Duh. I may be drunk but I'm not stupid. Her driver is waiting for her." He answered back. "come on, missy. Party's over!" he continued as he escorted Cath out of the club.

Gosh, I always forget how rich they really are. It's just so easy being with them, they're never boastful nor do they show off. I watched as Lance held Cath tightly, the straps of her purple Lanvin dress falling carelessly from her shoulders. Guess I never knew how much of a party animal she is. She blew me a kiss goodbye and I was in awe at how her diamond bangles glitter in the light.

I looked around the club and saw all the people in the dance floor. From this angle, they all look alike; clad in designer threads, wearing their highest heels, dancing with a handsome man, all of them having a great time.

I suddenly feel out of place in here. I may look different, what with me dressed to the nines, but inside I still feel the same. This isn't me. I don't belong here. This is not my world. Finally gathering the strength to stand up, I gathered my bag and stood up from the bar stool. I've had enough and I'm going home. If only I can find Hannah.

As I have guessed, it wasn't hard to find Hannah. She's exactly where I thought she would be- at the center of the dance floor. Is it just me or did her circle of friends expand more? I swear, they're forming a circle around her. Fighting off the dance floor divas, I finally made my way through where my sister is.

She's really beautiful, I think to myself. She's having the time of her life dancing, and she completely looks as if she was born to be here. I, on the other hand, look like an awkward twelve year old when I dance. Scary. She spots me and waves excitedly. "

"That's my sister!" she says excitedly "hey guys, look at my little sister. Isn't she beautiful?". She just like a kid actually. She's wide-eyed and giddy and I think she's really drunk. "join me, sistah." She continues.

"I'm going home. Wanna come with?"

"What? It's still early. The night is still you-you-young!"

Okay, she's definitely drunk.

"But I'm already tired. Come on." I said impatiently. I can't wait to lie in my bed and sleep.

"Ooh, you're no fun. Tell you what, you go ahead and I'll just see you at home."

"But how will you go home? Will you be okay?"

"Jess dear, I party every week. Give me some credit. Geez."

"Okay fine, but I'm done for tonight. I'll see you at home, okay?"

"Awww Jess. I'll miss you. Sure you don't want to stay?" she asked as she gave me a hug.

"Positive. You take care, okay?"

She merely nodded and pulled away. I watch her go back to where her friends are and decided to find Lance.

I was feeling tired, out of place, and drunk to notice where I'm actually walking. All I know is that I have to find Lance and then I can be safe in my room again.

"Ouch! Jesus Christ watch where your going!" a deep male voice interrupted.

I looked up and found brown eyes staring right back at me. I don't know what the hell happened but after just a few seconds my vision went from staring at blue eyes to staring at something that's all black. What the? I then realized that the black thing I was seeing was actually shirts. Yes, t-shirts worn by three bouncers in between me and blue eyes. Okay. That's weird.

Things went too fast and the next thing I knew, blue eyes was being escorted away from me and one of the bouncers shot me a dirty look. What did I do? I said I was sorry. Stupid annoying guy. What is he, like the clubs owner? Some VIP. They think they could just treat people like that. He totally overreacted! What a jerk. Well he can have the whole club for all I care. I mean three bouncers? Who does that? Pathetic losers, I tell you.

I spot Lance across the point where I was standing and his mouth was hanging open. Oh my god. What happened? Is it Cath? I run to him (at least I think it was running. My heels really hurt by now) and immediately panicked.

"Lance. Talk to me. What happened? Is it Cath? Oh god. Is she okay? Jesus. Oh god. What happened.. Oh my-"

"What? How did Cath get into this? Are you really that drunk? I'm supposed to ask _you _that question."

"Me? Why? What did I do?"

"You bumped him! As in total body contact. Oh my god. I can't believe it."

"What? Who? The jerk? With brown eyes? How'd you know him?"

"Don't you have a life? Oh my god, that's Chuck Bass! You know, as in _Chuck Bass_."

"Sorry, I don't know him."

"Yeah right. I only talk about him like, 80 percent of the time. Seriously Jess. Gossip Girl. N's best friend, B's true love, S' step-brother. Of course you know him!"

Of course I totally know him. I just don't want people to know that I read Gossip Girl. Everyone in school does, and treats these kids like New York royalty. I don't want to turn into a fan/obsessed/stalker type. Now that I think about it, I should've realized right away that it was him. Who would forget those brown eyes?

Me, apparently. Am I not the biggest loser?

**XOXO**

I decided to stay after all, mostly because of Lance. He said we should celebrate my "first physical contact" with a male. Haha. Please, like I've never gotten close to a male before.

Okay, so maybe I haven't. But who cares? We ordered two more margaritas and before I could even drink mine, it slipped again. Yes, that's glass number five tonight.

"My god woman, get a grip."

"Sorry, sorry. I told you I should've just gone home."

It was already about one thirty and you could tell from the way I look that I am way too plastered already. Lance paid for our drinks (and my fifth broken glass. Note to self: pay him) and I could tell that he didn't want to be with me anymore. He was looking around the club, eyeing the people everywhere.

"Lance. If you're looking for other friends, you can go to them. I'll be fine. I'm leaving anyway."

"Aww baby. I know this is going to sound crazy, but I think I just saw the man of my dreams pass by." He said, biting his lip guiltily.

"You mean Chuck Bass?"

"No.. a different guy."

"Well then go! Look for him. Find your happiness!"

"But what about you? I can't leave you. Forget it. I don't think he'll like me anyway."

"Nooo. You have to go find him. I'm fine, promise."

"Are you sure?"

"Of course. Now go before you even lose track of him."

"Thanks, Jess. I owe you. Before you leave, let me buy you another drink." He said then kissed my cheek. "give her whatever she wants, it's on me." He added to the waiter.

I really wish he'd find the guy. Lance is one of the nicest people I know and I really want to see him happy. He deserves it.

I ordered another margarita and just rested my elbow on the bar. I was tapping my fingers along to the music and kind of swaying in my seat. I just love club songs. The song ended and the intro of one of my favorite Pussycat dolls song played..

"Baby won't you take me out of this club, I wanna be with you.." crooned the Pussycat dolls

My margarita came shortly after and this time Barry, the waiter, served it to me in a plastic cup. Wow. That's clever. I have to be the lamest club go-er ever. I can't even handle holding a glass of alcoholic beverage. Yeah, Jessica Gregory, real nice.

"Plastic cups, huh? That's original. "said a voice I half recognized. I looked behind me and true enough, there it was.

A pair of piercing brown eyes, looking directly at me.

**XOXO**

A/N: Hey guys. Thanks for all the alerts. I do hope you review. I'm starting to lose hope in this story :( But I totally love the concept. It's gonna be good, promise. Reviews, okay? Thanks much!


	4. Chapter 3: Baby, I'm Bad News

**Chapter Three: Baby, I'm Bad News**

_Still Jess's POV_

I don't ever want to get up.

That was the first thing that entered my mind when I woke up. I was lying in the comfiest bed ever, it's all white sheets like big and puffy cotton balls. I could stay here forever.? Oh god, but my head hurts like crazy. What happened last night? More importantly, where the hell am I?

I looked around and saw an unfamiliar room. What a way to wake up in the morning. I try to get up and regret it afterwards. It's too painful to even move. My head is literally pounding and I really think my brain is going to bust out of my head any second now. And my body.. oh my god, it's sore. I feel like the weight of the whole world has been cast on me. Every part of me aches. As in everything.

What the hell happened? Something about last night.. something I don't quite remember. What did I do yesterday? Hmm.. let's see.. I woke up.. cooked lunch for Hannah, I did my homework.. started working on my term paper.. and went out with Hannah.

Oh my god.

Suddenly, flash backs of the night filled my brain. The club, my friends, drinking, broken glasses, and meeting this guy.

Chuck Bass.

I remember talking to him a bit (or was it flirting?), Then he asked me to dance. And then we ordered some more drinks, and then..

Nooo.. that can't be right. He asked me if I wanted to get out of the club. Did I say yes? I can't even remember. This is so unlike me, to forget such things. I knew it, I should've gone home when I had the chance to. Now I feel so disoriented.

Did I really do what I think I did? I close my eyes and try to think back on the other events that happened last night. Lips.. I remember lips. It was my first real kiss. We were inside the bar.. on the dance floor.. Oh god. How could I forget that. And then he took my hand.. led me out..

I remember lights.

Apparently someone famous was in the club too and the paparazzi were everywhere. We went out via the back door since apparently, Chuck owns Victrola. He even gave me a scarf to shield me from the harsh lights of the paparazzi. We took his limo and somehow we wound up at his penthouse. Some posh building in the Upper East Side.

We had drinks.. and then he gave me a tour of the place.. we went to his room and..

Oh my god. I am such a slut.

How could I have done that? I'm Jessica Gregory for christ's sake. I'm the boring one, the girl who could never do anything wrong. But wait.. maybe nothing happened? Maybe I passed out or something. Chuck is a gentleman so he let me sleep here..

I try hard to convince myself that nothing really happened, but at the back of the my mind I know something really did.. I just can't remember all the details but I felt it.. his lips on mine, taking our clothes off.. when he entered me. It was my first time, trust me, a girl knows. I feel really awful. Both physically and emotionally. What am I doing? I should've known better.. Shit. This is horrible.. God, what a mess..

"Oh good, you're already up." A voice suddenly says.

It's Chuck, looking at me with an expression I couldn't figure out.

He's looking incredibly sexy today, I can't help but notice. He appears to have just stepped out of the shower. His blond hair dripping wet, and his half naked body glistening with beads of water. The only thing that covers him is a towel.

"God, please dress up. Don't you think that's a little bit too personal?" I said.

"Babe, I think we're way past personal now."

So I had sex with him. Somehow that statement confirms my suspicions. Great. Just great.

"And" he added. "you might want to look at yourself. Hell, you're even more naked than I am!"

I gathered the guts to look under the tangled sheets, and sure enough, he was right.

The only thing that kept Chuck from seeing my naked body are his white comforter that is tangled in my body.

Shit.

He went back to the bathroom and when he returned, he was fully dressed already.

"You're still lying there?" he asked.

"Yeah, I can't quite move. My body is sore all over.."

"Well, you might want to get dressed already. I don't have time for this."

That was cold. Clearly the night meant nothing to him. It was just about sex. And now that he's had it, he doesn't care. Well, what did I expect anyway? He's Chuck Bass. He's notorious for this.

I got dressed and hurried out his room. I found him eating breakfast, and not once did he even glance at me. I just stood there, perhaps waiting for something. Like small talk or anything. The worst part was saying goodbye. Seriously. What do you do when the dreaded morning after comes? Do you kiss? Do you hug and give a polite kiss on the cheek? Do you shake hands like businessmen closing deals?

"You can let yourself out." He said coldly, still not bothering to look at me.

Fine. So he doesn't want anything to do with me. Just as I was about to open my mouth to say something, he suddenly spoke.

"Oh I get it. How much do you need for last night?"

That's when I felt like crying. He thinks I'm a whore he can just pay for giving him a good time?

"You know what, I thought you were better than that. I'm not a cheap prostitute you're used to fucking. I don't need your money." And with that, I stormed out of his apartment.

I was fighting back the tears from falling. I'd save that for later. On the outside, it appears as though I'm calm and composed. On the inside though, it is the complete opposite. I am embarrassed, in shock, and disgusted with myself. How could I have let something like this happen? What if I get pregnant? Oh god.

No, no. Chuck is notorious for being a ladies man. Surely he has taken proper precautions. No, pregnancy is out of the question. I feel like such a whore. A slut. An easy lay. Who would've thought that I would lose my virginity in a one night stand? Clearly, that's what this is, right? He was my first. First kiss, first everything. But he isn't my first love. It was just sex. Without the love.

I felt another batch of tears ready to fall.

I managed to get out of the building and started to look for a taxi. It's 9 in the morning, and people are already up and about. I notice that somehow people were staring at me and I remembered that I am still in my clothes from last night. Oh god. I didn't realize they look so whore-ish in the day. I didn't even check myself in the mirror before I left. I feel like my eyeliner is smudged and my red lipstick is all over my face from making out.

I look every inch of a woman who just had a one night stand.

I have the messy hair, lips dry from all the kissing, squinty eyes from the lack of sleep. I probably even smell like sex. Eww. I hailed a cab and sat quietly while tears streamed down my face. It's still a good 20 minutes or so until I reach home and I cannot face Hannah looking like this.

"Rough night?" the cab driver asks.

"Yeah."

"It's gonna be okay. Don't sweat it."

"Thanks."

I hurriedly pulled out the wet wipes I have in my purse and compose myself. I bet Hannah is still in bed, so there's no point explaining where I've been. Finally, the taxi reaches my house and I give the driver a little tip for being so nice to me.

I found my keys and opened the door as quietly as I can. Good thing there isn't really a parent home or else I'll probably be dead meat. I remove my shoes and immediately go straight to the staircase. I just wanna be in bed and sleep. And wish that my pillow has a life of its own so it can smother me to death.

I was going up the stairs when a I noticed a figure behind me. I feel so nervous that I can't even turn around to see who she is. Before I could even move, the figure suddenly talked.

"Where have you been?" my sister's high-pitched saccharine sweet voice demands.

This is bad. She doesn't get up this early. Especially after a night of partying.

"I'm talking to you, Jessica. Where the hell have you been?"

She called me Jessica. This is awful. Oh god.

"I stayed over at Cath's.. she passed out and I took care of her.. and I didn't realize I fell asleep.." I said before I could even stop myself.

"You could've called, you know. Or texted. Why didn't you answer any of my calls?" sounding a bit calmer already.

"Dead batt. Look, I'm sorry I got you worried."

"You should be. Oh god Jess. I was worried sick.. I thought something bad happened to you.."

"Hannah, I can handle myself. You know I don't do stupid things."

Yeah, nice one Jess. You just did the most stupid thing a girl could ever do. You slept with a guy you barely new. You gave him your virginity. Never mind if the guy was hot, or even famous. The fact remains.

"I know. I was just worried. I trust you, you know? You're the rational one. You don't just sleep with random strangers. Haha." She joked.

On normal days, I would just laugh at the joke. Today isn't a normal day.

"Want coffee?"

"No. I wanna sleep. But warm milk would be nice." I said.

"Okay. I'll make one for you. Poor baby sis had a rough night.."

I sat down our small dinner table while Hannah prepared my milk. I look at her and feel cheated. How can she look fresh in the morning? Unfair. She drank more! She partied harder! But she looks better. Ugh.

"Oooh, this reminds me. Oh my gosh, you would never believe who I saw in the club.. Seriously. You know that site we really love? Gossip Girl? Chuck Bass was there.. you should've seen him.. he was sizzling.."

Oh no. I don't think I can handle any more Chuck talk.

**XOXO**

"You are sooo busted." Lance said as soon as I picked up the phone.

"What the hell are you talking about?" It was six in the evening already, and my hangover is finally gone. I am now lying in bed, staring at the ceiling.

"You and Chuck Bass. Oh my gosh, you totally did it!" he said excitedly.

Whaaaat? How did he know that? Did he see me? Impossible.

"What are you talking about?" I asked while giving a little laugh.

What should I do? Tell him? No way. I don't want him to think of me as a slut.

"There's no point in lying, you know."

"Oooh, tell me what happened with your dream guy.." I said in an attempt to get the topic off Chuck.

"Jessica Gregory don't you dare change the topic. You slept with Chuck and you're not telling me."

I can feel him pouting at the end of the line, like how he always does when he's desperate to hear new gossip. There's really no point in denying, is there? I suppose I should tell him.

"Okay fine. So what if I did? How did you know by the way? Were you spying on me?"

Silence.

"Lance, how did you know? Tell me!"

"Lucky guess?"

"Yeah right. Come on spill. How did you know?"

Why won't he tell me? One minute he's acting so excited, and the next minute he goes all quiet on me. He knows the secret now and I think I deserve to know how he found out.

"Well? I'm waiting."

"Honey.. it's all over Gossip Girl."

Whaaat? It's on Gossip Girl? Oh my god. I am so busted. What will I do? What will I do? Blair will eat me alive. Oh my god. I can't go to school. I can't face everyone. Especially Blair Waldorf.

**XOXO**

_**A/N: Hey people. What did you think of this chapter? I really hope you guys review. Thanks and much love.**_


	5. Chapter 4: With Eyes Closed

**Chapter Four: With Eyes Closed**

_**Jess's POV **_

"Finally my life is getting back to normal" I said as soon as I saw my friends after school.

"What do you mean?" Cath asked while combing her already perfectly combed hair.

"My life. I no longer feel like Blair is out to get me or something."

"Duh, well you shouldn't. You didn't do anything to piss her off, right?"

Silence. Lance and I just looked at each other.

"Right." We both said at the same time.

The past few months has been hard for me. I always felt like I should watch my back or something. But now, at last, I can breathe. It's been quite a while since the incident with Chuck (and Lance is actually the only person who knows about it) and I decided to put it all behind me. The picture in Gossip Girl was nothing major; I was covered in a bundle of scarves. Lance recognized me because of the dress, and I'm sure no one else has recognized me. And why would they? It's not like they actually pay attention to me or whatever.

Chuck and Blair are officially the hottest couple in school and I could care less. Chuck was a mistake even though he was my first. Let Blair have him. With his womanizing ways and the way he treated me the morning after? Geez, I don't even want to belong in that kind of world.

"Sooo, what are we doing this weekend?" asked Cath, still oblivious to the fact that Lance and I are keeping a secret from her.

"I don't know. Maybe a girls only sleepover. Oh my good, it will be major!" said Lance.

"Girls only? You do know that means no Lance too, right?" Cath hinted.

"You're a bitch." He said in his most girly and whiny tone.

"And you're gay."

"Yeah, coz I'm happy! Gay means happy. So honey, everybody is gay!" was Lance's funny reply.

Somehow I wasn't in the mood for chit chat. Or anything else. I just felt sleepy.. and sick.

"Hey Jess, are you okay?" asked Cath.

"Yeah. I just feel a little sleepy. And nauseous. I totally crammed my Literature paper and I have zero sleep."

Lance looked at me with a concerned expression. I ignored him.

"Well you should get some sleep. And stay off the coffee. Now, I have to go. I promised mother I would help her choose her dress for the gala tomorrow night." Cath said as she kissed us goodbye.

Okay. I am totally dreading this, being alone with Lance. Something in his expression tells me that he's going to tell me something awful.

"Look Jess, don't freak out or anything, okay? Just hear me out.."

"Okaaaay…"

"You know you and I have always been friends.."

I hate that line. Somehow that's the line that signals a bad news is about to be dropped..

"Yess…"

"And you know I love you, that I'm concerned about you.."

"Uh-huh.."

I don't like where this conversation is going. Not at all.

"So you don't mind me asking.. when did you last get your period?"

Oh god. The dreaded question.

"I don't know, I don't really keep track. I have an irregular cycle. What does that have to do with anything?!" I asked, even though I know perfectly the reason behind it.

"Hmm.. there's no easy way of saying this but.. have you tried taking a pregnancy test yet?"

"No. Why? I don't need that. I don't even have an active sex life!"

"But.."

"Lance come on. Me? Get pregnant? No way. Can we just leave it?"

"Fine. But I still think you should take a test to be sure."

No need. I am soo not pregnant. I mean I can't be. I just had sex once. That's like, impossible. Right?!

**XOXO**

So maybe I wanted to prove Lance wrong, that's why I immediately agreed when he told me that we should buy a pregnancy test. The next day, we were armed with disguises. Actually, it was all Lance's idea. We had the works; scarves, layers of clothes, huuuuge sunglasses. Somehow we ended up in a drugstore in Fairfield, Connecticut.

Crazy, I know. But that's the fun thing with being friends with Lance, it's never boring. I asked him why go somewhere really far just for a pregnancy test that I'm sure to be negative anyway. He said he's pretty sure Gossip Girl won't be in Fairfield and so that rumors will be avoided.

I suppose he was right. We bought 10 pregnancy tests, guaranteed to give "the best and most accurate results" says in the box. Although I was just laughing it all off and not taking anything seriously, deep inside I was falling apart. I didn't know what to expect. The bigger part of m says that there's nothing to worry about, I'm sure Chuck took care of all the precautions beforehand. He's the expert, after all. And yet, a part of me feels uncertain. What if I get pregnant?

Oh god, my whole world will collapse. What will I feed the baby? How will my parents react? Where will we live? Will Chuck stand by me? What will Blair do? So many questions.

Okay. Relax. Everything will be okay, I told myself. I was on the six pregnancy test now but I didn't bother to look at the other results. Not yet. I can't bear to look.

"So, what did it say?" asked Lance. I was on the telephone with him, both of us anxiously awaiting the results.

"Well, go and have a look."

"I can't. I'm too nervous."

"Me too. My hands are shaking. Gosh, this is worse than waiting for our College Admissions Results." Leave it to Lance to make the situation lighter.

After my last pregnancy test, I waited for another five minutes. Neither of us were talking. I guess we were both really really nervous.

Okay fine. I'm going to take a look.

"Lance. I'm going to take a look."

"Good luck, sister."

With eyes closed, I turned all the pregnancy tests around.

"Well? Well?" Lance asked impatiently.

"My eyes are closed. I can't do this."

"Come on, Jess. Get it over with."

"But I can't."

"Of course you can. I'll be here. Come on."

Fine. I opened my eyes and just stood there.

"Jess. Talk to me. Go."

"I'm going to call you back later.."

"What? Jessica Gregory, don't you fucking dare – " but I clicked it before he could even finish.

There they were, the tests that determined my future. Ten pregnancy tests looking back at me, each containing the same thing: two pink lines.

Oh god. No. This can't be happening.

**XOXO**

**A/N: I know this is kinda shrot. But this is the last chap with Jess's POV for now. Ready for some Chair action? Reviews are love :) Thanks to those who are really taking time to review. Super appreciate it! xoxo**


	6. Chapter 5: Have I Told You

_A/N: Thanks for the reviews. Really appreciate it. Anyhow, this is my version of Season 3. This kicks off just right after the last episode of Season 2. But the timing is different. Beginning this chapter, they still have 3 months before graduation. Like I promised, some Chair action in this chapter. Mostly fluff, but I know we love that stuff right :P_

_Disclaimer: I do not own Gossip Girl or any of the characters. (But I do own the new characters introduced, namely Jess, Hannah, Lance, and Cath)_

XOXO

**Chapter Five: Have I Told You**

Blair's POV

"Good morning, Dorota!" I said as Dorota went inside my room to let the sunshine in.

"Miss Blair. You up early." She replied, obviously surprised.

I can't say I blame her, though. It _is _very early. Nine o'clock on a Saturday morning and I'm already up? Now that's a first.

"Today is a special day, Dorota. Have you forgotten what day it is?"

No, it's not my birthday. And no, it's not Christmas either. Today is a special day because it marks the second month of Chuck and I in coupledom. Yes, you heard that right. Two months of bliss and ecstasy with Chuck Bass. I didn't even think that was possible.

But I'm not complaining. For once, everything was working out with Chuck and I wouldn't have it any other way. Chuck Bass loves me. I, Blair Waldorf, am in love. This time I know it's for keeps. The thing I had with Nate was nothing. I think since we grew up together, he was kind of the comfort zone. I was just in denial for such a long time, I think.

Well, whatever. Chuck is the only man I love now. Who knew that the most heartless teenage boy in Manhattan could actually love? I don't even care that I'm not his "first", because now I know that I am his first AND last. That is soo much more romantic.

Don't get me wrong, he's pretty much the same asshole and pain in the ass that he is, but the difference now is that he's mine. He's my asshole, my pain in the ass.

My life is waaay better than any Audrey Hepburn movie. But I suppose I had it coming. Haven't I always known that my life will be perfect?

I got out of bed, showered, and put on a really really nice dress. All the while resisting the urge to call Chuck and greet him a happy monthsary. I want him to think that I've somehow forgotten it so he would be really delighted with my surprise later. And maybe if he thought I forgot, he would go all out and buy me a really huge surprise present. Who knows what could happen?

"Miss Blair, the car is waiting for you downstairs."

"Very well, Dorota. Do you have the vintage candelabras with you?"

"Yes Miss Blair, along with the fine china you ordered."

"Okay. Now let's go! We have a lot to do."

Lunch hasn't even come and yet I was preparing for dinner already. But it isn't just any other dinner, it's _the_ dinner. I was finally getting in touch with my inner domestic side and cook a romantic dinner for two. Tell me, how wife material is that? But before anything else, I have to head over to Chuck's and deliver these candelabras and china. Of course, I must brief his house staff as well as to what will happen tonight.

Thank god Lily is away for the weekend. She was visiting her sister Carol in Miami. And she's busy with the whole wedding arrangement and stuff. I knoow, she's getting married again! To Ruffus of all people. But whatever, I just hope that this would be the last time.

I have to make sure Chuck isn't home. Well, he probably isn't but still. I know he's busy learning the ropes to Bass Industries and that's another reason why I want to surprise him. To get his mind off things and to relax. Tell me, am I not the perfect girlfriend?

I called Serena to make sure but instead I got her voicemail. "S, are you sure Chuck isn't home? I'm on my way over and I swear, if he's there, I am going to murder you. Okay, glad to have that settled. Love ya. Bye!"

Even though I asked Serena for like, a hundred times now, I can't help it. I want everything in our little night in to be perfect. I just want to spend a nice relaxing evening at home with my boyfriend. Maybe watch a nice, romantic DVD, eat a delicious meal by candlelight that I cooked. Well, okay, so maybe Dorota would be doing the cooking – but I'll be there. And I'm going to help, aren't I? Then maybe lots of crazy, passionate sex after. Mmm. I'm sure Chuck would love it, I know I would.

We reached his building and went immediately to his floor. I was expecting to find Serena, but no one was there except for the maids. Okay, good. I gave them very specific instructions and then dragged Dorota with me to my next mission.

I'm going to the grocery, something I once thought of as the most boring thing in the world. I can't help it if I didn't like stepping in and seeing all those detergents and cleaning tools lined up. But not anymore, I'm domesticated now. I'm wife material, and not just a trophy wife at that. Someday, I know I'll be Mrs. Chuck Bass. I just know it.

XOXO

By seven o'clock I was more than ready. My set of clothes, which I had delivered here in Chuck's building, was thoroughly examined and fitted. I decided on a beautiful pink dress by Eleanor Waldorf. It didn't scream "formal" but then I didn't want to look too casual either. My hair has been blow dried and in it's most natural state. I've been perfumed and cotton-budded all over until I was sure that I was absolutely picture perfect for Chuck.

I called his office and his secretary said he was on his way home already. I examined the fruits of my labor (Okay fine, Dorota's) and felt incredibly proud. I can't believe I slaved in the kitchen for all this. . It was a setting worthy of a Vogue feature. It looked just like how I imagined: the table, covered in a white and plum tablecloth, looked very beautiful. I arranged the utensils too. Dorota even folded the napkins into swans. The candelabras illuminated the setting very romantically too.

The best part was the food. Somehow, we managed (I mean they) to cook a four course meal in such a short time. Dorota is really heaven sent. Of course, Chuck's maid Janeena helped too. What can I say, culinary masterpieces are hard to create. So I didn't technically _cook_, but I tried! Almost everything I made/stirred/mixed/fried had to be redone by Dorota or Neena. I can learn, though. I guess. Who knew cooking could be so damn hard?

"Miss Blair, the doorman said Mr. Chuck has arrived. He is on his way here as we speak." Dorota said.

Well, it's about time! I told her to just sneak out later and that she can have a night off. Go to a bar or something. God knows she deserves it.

Finally I heard the elevator open and I heard Chuck's footsteps approaching. He didn't notice me at first, and he looked as though he was lost in deep thought. He was just standing by the barstool, ready to pour himself a drink I presumed.

"Well, Bass, aren't we a jerk today?"

He looked up and saw me, his expression unfathomable.

"Blair." He finally said.

"Were you expecting someone else?"

"No, of course not. Who else would I want to see? Come here.."

He took me in his arms and kissed me. Mmm..

"Happy second month, Chuck. You didn't think I forgot, right?"

"No.. not really. Happy second month, Waldorf." He said, giving me another kiss.

"Well, let's go to the kitchen.. I have a surprise for you.." I said, grabbing his hand. I could see that he was distracted, but he was trying very hard not to show me.

"Blair.." he said, pulling me to face him. I could tell he was about to say something, but quickly decided against it. Trust me, I know him better than anyone else does.

"Yeah?"

He looked deep into my eyes and I felt my heart melt. God, why does he have to be that sexy?

"I love you, Blair Waldorf. You're the only girl I've ever loved." He said in that unbelievably sexy voice he has.

"I love you more, Chuck Bass. Now let's go to the kitchen.. I have a surprise for you!"

"One more thing.." he continued. He pulled me closer before kissing me. "have I told you how much I love you?"

How can that not make me smile? Whatever it was that was bothering him, I was pretty sure it was off his mind at that moment. I led him to the kitchen and got ready for the most romantic night of my life.

XOXO

A/N: Wee. Did that or did that not make your heart melt? I swear, I couldn't stop smiling after writing that. I can just imagine Chuck saying that… Gooood, it's making me giddy all over!. Okay, reviews please :P


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